Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/20—Oxygen atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
  • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
  • A01N41/04—Sulfonic acids; Derivatives thereof
  • A01N41/06—Sulfonic acid amides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
  • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/14—Ectoparasiticides, e.g. scabicides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
  • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
  • C07D213/40—Acylated substituent nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/56—Amides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/68—One oxygen atom attached in position 4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to a novel pesticide. More specifically, the present invention relates to an aryloxyacetamide compound and an acaricide and/or insecticide containing the aryloxyacetamide compound as an active ingredient.
• the aryloxyacetamide compound has a superior acaricidal and/or insecticidal activity, superior safety, and can be synthesized advantageously and industrially.
• X 2 represents a hydrogen atom, halogen atom, C1-8 alkyl group or the like.
• R 6 represents a phenyl group, cyano group, C1-4 alkyl group or the like.
• R 10 represents a halogen atom or C1-4 alkyl group.
• X 3 represents a chlorine atom, bromine atom, or methyl group.
• Y 3 represents a chlorine atom, bromine atom, or methyl group.
• R 11 represents an ethyl group or n-propyl group.
• R 12 represents an ethyl group.
• R 13 represents an alkyl group, alkenyl group or the like.
• R 14 represents a benzyloxymethyl group or the like, in which the phenyl ring of the benzyl moiety is optionally substituted with a C1-4 alkoxy group.
• R 17 represents a C1-4 alkyl group, C3-6 cycloalkyl group or the like.
• Patent Document 2
• Patent Document 3
• an aryloxyacetamide compound having a specific structure, or salt thereof has a superior acaricidal and/or insecticidal activity, and may be used as an active ingredient of acaricides and/or insecticides having excellent properties and high safety.
• the present invention was achieved on the basis of this perception.
• the present invention is as follows:
• Cy represents a C6-10 aryl group, or a 5- to 10-membered heteroaryl group including 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, oxygen atom and sulfur atom.
• X is a substituent of Cy, and represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, amino group, unsubstituted or substituted C1-6 alkyl amino group, unsubstituted or substituted C1-7 acyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C1-6 alkoxysulfonyl group, unsubstituted or substituted C6-10 aryl group, 5- to 10-membered unsubstitute
• n represents the number of X bonded with Cy and represents an integer of 0 to 5.
• Xs may be the same as or different from each other.
• Xs may bond to form a ring together with the carbon atoms or nitrogen atoms of Cy, which bond with Xs.
• R 1a represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C1-6 alkoxy group, or unsubstituted or substituted C1-6 alkyl thio group.
• R 1b represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, or unsubstituted or substituted C2-6 alkynyl group.
• R 1a and R 1b may bond to form a ring together with the carbon atom bonded thereto.
• R 1a and R 1b may together form an unsubstituted or substituted exomethylene group.
• Z represents an oxygen atom or a sulfur atom.
• Q represents a group represented by formula (II) or formula (III):
• R 2 represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C1-7 acyl group, or unsubstituted or substituted C1-6 alkoxycarbonyl group.
• R 3 and R 4 independently represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C6-10 aryl group, 5- to 10-membered unsubstituted or substituted heteroaryl group including 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, oxygen atom and sulfur atom, or cyano group.
• R 3 and R 4 may bond to form a ring together with the carbon atom bonded thereto.
• R 5 represents a 5- to 10-membered unsubstituted or substituted heteroaryl group including 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, oxygen atom and sulfur atom.
• the aryloxyacetamide compound or salt thereof according to the present invention is able to prevent pesticides which are harmful to agricultural crops or harmful in terms of hygiene. Particularly, the aryloxyacetamide compound or salt thereof according to the present invention is able to prevent acaricides effectively.
• the aryloxyacetamide compound of the present inventions is a compound represented by formula (I).
• the term “unsubstituted” refers to a group being the only group serving as a mother nucleus.
• this description when there is no description of being “substituted” and a description is only provided for the name of the group serving as a mother nucleus, this refers to “unsubstituted” unless specifically indicated otherwise.
• substituted refers to any hydrogen atom or a group serving as a mother nucleus being substituted with a group having a structure that is the same as or different from the mother nucleus.
• a “substituent” is another group bonded with the group serving as the mother nucleus. There may be one substituent or two or more substituents. Two or more substituents may be the same as or different from each other.
• C1-6 indicates that the number of carbon atoms of the group serving as the mother nucleus is 1 to 6.
• the number of carbon atoms present in substituents is not included in this number of carbon atoms.
• a butyl group having an ethoxy group as a substituent thereof is classified as a C2 alkoxy C4 alkyl group.
• halogen atom such as a fluorine atom, chlorine atom, bromine atom, iodine atom or the like;
• a C1-6 alkyl group such as a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group or the like;
• a C3-8 cycloalkyl group such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group or the like;
• a C2-6 alkenyl group such as a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group or the like;
• a C3-8 cycloalkenyl group such as a 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group or the like;
• a C2-6 alkynyl group such as an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group or the like;
• a C1-6 alkoxy group such as a methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group or the like;
• a C2-6 alkenyloxy group such as a vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group or the like;
• a C2-6 alkynyloxy group such as an ethynyloxy group, propargyloxy group or the like;
• a C6-10 aryl group such as a phenyl group, naphthyl group or the like;
• a C6-10 aryloxy group such as a phenoxy group, 1-naphthoxy group or the like;
• a C7-11 aralkyl group such as a benzyl group, phenethyl group or the like;
• a C7-11 aralkyloxy group such as a benzyloxy group, phenethyloxy group or the like;
• a C1-7 acyl group such as a formyl group, acetyl group, propionyl group, benzoyl group, cyclohexyl carbonyl group or the like;
• a C1-7 acyloxy group such as a formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexyl carbonyloxy group or the like;
• a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group or the like;
• a C1-6 haloalkyl group such as a chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group or the like;
• a C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group or the like;
• a C2-6 haloalkynyl group such as a 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group or the like;
• a C1-6 haloalkoxy group such as a 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group or the like;
• a C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group, 3-bromobutenyloxy group or the like;
• a C6-10 haloaryl group such as a 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophenyl group or the like;
• a C6-10 haloaryloxy group such as a 4-fluorophenyloxy group, 4-chloro-1-naphthoxy group or the like;
• a halogen-substituted C1-7 acyl group such as a chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4-chlorobenzoyl group or the like;
• a C1-6 alkyl amino group such as a methyl amino group, dimethyl amino group, diethyl amino group or the like;
• a C6-10 aryl amino group such as an anilino group, naphthyl amino group or the like;
• a C7-11 aralkyl amino group such as a benzyl amino group, phenyl ethyl amino group or the like;
• a C1-7 acyl amino group such as a formyl amino group, acetyl amino group, propanoyl amino group, butyryl amino group, i-propyl carbonyl amino group, benzoyl amino group or the like;
• a C1-6 alkoxycarbonyl amino group such as a methoxycarbonyl amino group, ethoxycarbonyl amino group, n-propoxycarbonyl amino group, i-propoxycarbonyl amino group or the like;
• an unsubstituted or substituted aminocarbonyl group such as an aminocarbonyl group, dimethyl aminocarbonyl group, phenyl aminocarbonyl group, N-phenyl-N-methyl aminocarbonyl group or the like;
• an imino C1-6 alkyl group such as an iminomethyl group, (1-imino)ethyl group, (1-imino)-n-propyl group or the like;
• a hydroxyimino C1-6 alkyl group such as a hydroxyiminomethyl group, (1-hydroxyimino)ethyl group, (1-hydroxyimino)propyl group or the like;
• a C1-6 alkyl thio group such as a methyl thio group, ethyl thio group, n-propyl thio group, i-propyl thio group, n-butyl thio group, i-butyl thio group, s-butyl thio group, t-butyl thio group or the like;
• a C2-6 alkenyl thio group such as a vinyl thio group, allyl thio group or the like;
• a C2-6 alkynyl thio group such as an ethynyl thio group, propargyl thio group or the like;
• a C6-10 aryl thio group such as a phenyl thio group, naphthyl thio group or the like;
• heteroaryl thio group such as a thiazolyl thio group, pyridyl thio group or the like;
• a C7-11 aralkyl thio group such as a benzyl thio group, phenethyl thio group or the like;
• a (C1-6 alkyl thio)carbonyl group such as a (methyl thio)carbonyl group, (ethyl thio)carbonyl group, (n-propyl thio)carbonyl group, (i-propyl thio)carbonyl group, (n-butyl thio)carbonyl group, (i-butyl thio)carbonyl group, (s-butyl thio)carbonyl group, (t-butyl thio)carbonyl group or the like;
• a C1-6 alkyl sulfinyl group such as a methyl sulfinyl group, ethyl sulfinyl group, t-butyl sulfinyl group or the like;
• a C2-6 alkenyl sulfinyl group such as an allyl sulfinyl group or the like;
• a C2-6 alkynyl sulfinyl group such as a propargyl sulfinyl group or the like;
• a C6-10 aryl sulfinyl group such as a phenyl sulfinyl group or the like;
• heteroaryl sulfinyl group such as a thiazolyl sulfinyl group, pyridyl sulfinyl group or the like;
• a C7-11 aralkyl sulfinyl group such as a benzyl sulfinyl group, phenethyl sulfinyl group or the like;
• a C1-6 alkyl sulfonyl group such as a methyl sulfonyl group, ethyl sulfonyl group, t-butyl sulfonyl group or the like;
• a C2-6 alkenyl sulfonyl group such as an allyl sulfonyl group or the like
• a C2-6 alkynyl sulfonyl group such as a propargyl sulfonyl group or the like;
• a C6-10 aryl sulfonyl group such as a phenyl sulfonyl group or the like;
• heteroaryl sulfonyl group such as a thiazolyl sulfonyl group, pyridyl sulfonyl group or the like;
• a C7-11 aralkyl sulfonyl group such as a benzyl sulfonyl group, phenethyl sulfonyl group or the like;
• a 5-membered heteroaryl group such as a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group or the like;
• a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group or the like;
• a condensed heteroaryl group such as an indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group or the like;
• a saturated heterocyclic group such as an aziridinyl group, oxiranyl group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group or the like;
• a tri C1-6 alkyl-substituted silyl group such as a trimethyl silyl group, triethyl silyl group, t-butyl dimethyl silyl group or the like;
• Cy represents a C6-10 aryl group or a heteroaryl group.
• the “C6-10 aryl group” may be a monocyclic ring, or a polycyclic ring in which the rings bond with each other.
• the polycyclic aryl group as long as at least one aromatic ring is included, other rings may be a saturated alicyclic ring, an unsaturated alicyclic ring or an aromatic ring.
• the C6-10 aryl group include a phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group or the like.
• heteroaryl group is a 5- to 10-membered aryl group which has, other than carbon atoms, 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, oxygen atom and sulfur atom as the atoms constituting the ring.
• the heteroaryl group may be a monocyclic ring, or a polycyclic ring in which the rings bond to each other.
• heteroaryl group examples include a 5-membered heteroaryl group, 6-membered heteroaryl group, condensed heteroaryl group or the like, which are listed as the examples of the “substituent”.
• Cy is preferably a phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, or quinoxalinyl group, and more preferably a phenyl group.
• X represents a substituent of Cy
• X represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, amino group, unsubstituted or substituted C1-6 alkyl amino group, unsubstituted or substituted C1-7 acyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C1-6 alkoxysulfonyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted
• n represents the number of X of Cy, and represents an integer of 0 to 5.
• Xs may the same as or different from each other.
• Xs may bond to form a ring together with the carbon atoms or nitrogen atoms, which bond with Xs.
• the “C1-6 alkyl group” of X may be a linear alkyl group or a branched alkyl group.
• the alkyl group include a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methyl butyl group, 2,2-dimethyl propyl group, i-hexyl group or the like.
• a C3-8 cycloalkyl C1-6 alkyl group such as a cyclopropyl methyl group, 2-cyclopropyl ethyl group, cyclopentyl methyl group, 2-cyclohexyl ethyl group, 2-cyclooctyl ethyl group or the like;
• a C1-6 haloalkyl group such as a fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-tolufluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethyl ethyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group or the like;
• a hydroxy C1-6 alkyl group such as a hydroxymethyl group, 2-hydroxyethyl group or the like;
• a C1-6 alkoxy C1-6 alkyl group such as a methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group or the like;
• a C2-6 alkenyloxy C1-6 alkyl group such as a vinyloxymethyl group, allyloxymethyl group, propenyloxymethyl group, butenyloxymethyl group or the like;
• heteroaryloxy C1-6 alkyl group such as a pyridine-2-yloxymethyl group or the like
• a C1-7 acyl group such as a formyl group, acetyl group, propionyl group or the like;
• a C1-7 acyloxy C1-6 alkyl group such as a formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group or the like;
• a carboxyl group C1-6 alkyl group such as a carboxyl methyl group, carboxyl ethyl group or the like;
• a C1-6 alkoxycarbonyl C1-6 alkyl group such as a methoxycarbonyl methyl group, ethoxycarbonyl methyl group, n-propoxycarbonyl methyl group, i-propoxycarbonyl methyl group or the like;
• a C1-7 acyl amino C1-6 alkyl group such as a formamide methyl group, acetamide methyl group, 2-acetamide ethyl group, propionyl aminomethyl group, propionyl aminoethyl group or the like;
• a C1-6 alkyl aminocarbonyl C1-6 alkyl group such as a methyl aminocarbonyl methyl group, ethyl aminocarbonyl methyl group, i-propyl aminocarbonyl methyl group, t-butyl aminocarbonyl methyl group, s-butyl aminocarbonyl methyl group, n-pentyl aminocarbonyl methyl group or the like;
• a C1-6 alkoxycarbonyl amino C1-6 alkyl group such as a methoxycarbonyl aminomethyl group, ethoxycarbonyl aminomethyl group, i-propoxycarbonyl aminomethyl group, t-butoxycarbonyl aminomethyl group, s-butyloxycarbonyl aminomethyl group, n-pentyloxycarbonyl aminomethyl group or the like;
• a C7-11 aralkyl group such as a benzyl group, phenethyl group or the like;
• a C6-10 aryl carbonyl amino C1-6 alkyl group such as a benzoyl aminomethyl group or the like; and the like.
• Examples of the “C3-8 cycloalkyl group” of X include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and the like.
• Examples of the “C2-6 alkenyl group” of X include a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
• Examples of the “substituted C2-6 alkenyl group” include a C2-6 haloalkenyl group and the like, such as a 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group or the like.
• C2-6 alkynyl group examples include an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like.
• Examples of the “substituted C2-6 alkynyl group” include a C2-6 haloalkynyl group and the like, such as a 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group or the like.
• Examples of the “C1-6 alkoxy group” of X include a methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
• Examples of the “substituted C1-6 alkoxy group” include a C1-6 haloalkoxy group and the like, such as a chloromethoxy group, dichloromethoxy group, difluoromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group or the like.
• Examples of the “C1-6 alkylamino group” of X include a methyl amino group, dimethyl amino group, diethyl amino group and the like.
• Examples of the “C1-7 acyl group” of X include a formyl group, acetyl group, propionyl group, benzoyl group and the like.
• substituted C1-7 acyl group examples include a halogen-substituted C1-7 acyl group and the like, such as a chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4-chlorobenzoyl group or the like.
• Examples of the “C1-6 alkoxycarbonyl group” of X include a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group and the like.
• Examples of the “substituted C1-6 alkoxycarbonyl group” include a C3-8 cycloalkyl C1-6 alkoxycarbonyl group such as a cyclopropyl methoxycarbonyl group, cyclobutyl methoxycarbonyl group, cyclopentyl methoxycarbonyl group, cyclohexyl methoxycarbonyl group, 2-methyl cyclopropyl methoxycarbonyl group, 2,3-dimethyl cyclopropyl methoxycarbonyl group, 2-chlorocyclopropyl methoxycarbonyl group, 2-cyclopropyl ethoxycarbonyl group or the like;
• a C1-6 haloalkoxycarbonyl group such as a fluoromethoxycarbonyl group, chloromethoxycarbonyl group, bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group, tri chloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, pentafluoroethoxycarbonyl group, 4-fluorobutoxycarbonyl group, 3,3,3-trifluoropropoxycarbonyl group, 2,2,2-trifluoro-1-trifluoromethyl ethoxycarbonyl group, perfluorohexyloxycarbonyl group or the like; and the like.
• Examples of the “C1-6 alkylthio group” of X include a methyl thio group, ethyl thio group, n-propyl thio group, n-butyl thio group, n-pentyl thio group, n-hexyl thio group, i-propyl thio group or the like.
• Examples of the “substituted C1-6 alkylthio group” include a C1-6 haloalkyl thio group and the like, such as a trifluoromethyl thio group, 2,2,2-tolufluoroethyl thio group and the like.
• Examples of the “C1-6 alkyl sulfonyl group” of X include a methyl sulfonyl group, ethyl sulfonyl group, t-butyl sulfonyl group and the like.
• Examples of the “substituted C1-6 alkyl sulfonyl group” include a C1-6 haloalkylsulfonyl group and the like, such as a trifluoromethyl sulfonyl group, 2,2,2-tolufluoroethyl sulfonyl group or the like.
• Examples of the “C1-6 alkoxysulfonyl group” of X include a methoxysulfonyl group, ethoxysulfonyl group, t-butoxysulfonyl group and the like.
• Examples of the “C6-10 aryl group” and “heteroaryl group” of X are the same as the examples of Cy.
• halogen atom such as a fluorine atom, chlorine atom, bromine atom, iodine atom or the like;
• a C1-6 alkyl group such as a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group or the like;
• a C1-6 haloalkyl group such as a chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group or the like;
• hydroxyimino C1-6 alkyl group examples include a hydroxyiminomethyl group, (1-hydroxyimino)ethyl group, (1-hydroxyimino)propyl group and the like.
• Examples of the “substituted hydroxyimino C1-6 alkyl group” include a C1-6 alkoxyimino C1-6 alkyl group such as a methoxyiminomethyl group, (1-methoxyimino)ethyl group, (1-methoxyimino)propyl group, ethoxyiminomethyl group, (1-ethoxyimino)ethyl group, (1-ethoxyimino)propyl group or the like; a C3-8 cycloalkyl C1-6 alkoxyimino C1-6 alkyl group such as a (1-cyclopropyl methoxyimino)ethyl group or the like; a C7-11 aralkyloxyimino C1-6 alkyl group such as a benzyloxyiminomethyl group, (1-benzyloxyimino)ethyl group or the like; and the like.
• a C1-6 alkoxyimino C1-6 alkyl group such as a
• halogen atom examples include a fluorine atom, chlorine atom, bromine atom, iodine atom and the like.
• Examples of the ring formed by bonding Xs together with the carbon atoms or nitrogen atoms bonded thereto include a cyclopentene ring, cyclohexene ring, 3,4-dihydro-2H-pyran ring, 3,4-dihydro-2H-thiopyran ring, 3,4-dihydro-2H-thiopyran 1,1-dioxide ring and the like.
• R 1a represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C1-6 alkoxy group, or unsubstituted or substituted C1-6 alkyl thio group.
• C1-6 alkyl group examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group” and “C1-6 alkyl thio group” of R 1a are the same as the examples of X described above.
• R 1a is preferably a C1-6 alkyl group.
• R 1b represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, or unsubstituted or substituted C2-6 alkynyl group.
• R 1a and R 1b may bond to form a ring together with the carbon atom bonded thereto.
• Examples of the ring formed by bonding R 1a and R 1b together with the carbon atom bonded thereto include a cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring and the like.
• Examples of the “substituted exomethylene group” formed by R 1a and R 1b together with the carbon atom bonded there to include a C1-6 alkyl-substituted exomethylene such as an ethylidene group, isopropylidene group or the like.
• Q represents a group represented by formula (II) or formula (III).
• R 2 represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C1-7 acyl group, or unsubstituted or substituted C1-6 alkoxycarbonyl group.
• R 3 and R 4 independently represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted heteroaryl group, or cyano group.
• R 3 and R 4 may bond to form a ring together with the carbon atom bonded thereto.
• R 3 and R 4 are preferably a C1-6 alkyl group.
• the ring formed by bonding R 3 and R 4 together with the atom bonded thereto includes a cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, oxirane ring and the like.
• R 5 represents an unsubstituted or substituted heteroaryl group.
• heteroaryl group examples include a 5-membered heteroaryl group such as a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group or the like;
• a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group or the like;
• a condensed heteroaryl group such as an indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group or the like;
• a partially unsaturated 5-membered heterocyclic group such as a pyrrolinyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, thiazolinyl group or the like; and the like.
• heteroaryl group As the “heteroaryl group” of R 5 , a pyridyl group is preferable.
• substituents of the “substituted heteroaryl group” of R 5 include the following substituents:
• halogen atom such as a fluorine atom, chlorine atom, bromine atom, iodine atom or the like;
• a C1-6 alkyl group such as a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group or the like;
• a C3-8 cycloalkyl group such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group or the like;
• a C2-6 alkenyl group such as a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group or the like;
• a C2-6 alkynyl group such as a ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group or the like;
• a C1-6 alkoxy group such as a methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group or the like;
• a C6-10 aryl group such as a phenyl group, naphthyl group or the like;
• a C1-6 haloalkyl group such as a chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group or the like;
• a C6-10 haloaryl group such as a 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophenyl group or the like;
• a 5-membered heteroaryl group such as a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group or the like;
• a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group or the like;
• R 6 and R 7 independently represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C6-10 aryl group, or unsubstituted or substituted heteroaryl group.
• R 6 and R 7 may bond to form a ring together with the sulfur atom bonded thereto.
• R 6 and R 7 examples of the “unsubstituted or substituted C1-6 alkyl group”, “unsubstituted or substituted 3-8 cycloalkyl group”, “unsubstituted or substituted C2-6 alkenyl group”, and “unsubstituted or substituted C2-6 alkynyl group” of R 6 and R 7 are the same as the examples of X described above.
• halogen atom fluorine atom chlorine atom, bromine atom, iodine atom or the like
• a C1-6 alkyl group methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group or the like;
• a C1-6 haloalkyl group chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group or the like;
• Examples of the ring formed by bonding R 6 and R 7 together with the sulfur atom bonded thereto include a tetrahydrothiophene ring, tetrahydrothiopyran ring, oxathiane ring and the like.
• Z represents an oxygen atom or sulfur atom, and preferably represents an oxygen atom.
• aryloxyacetamide compounds of the present invention a compound wherein Cy in formula (I) represents a phenyl group, R 1b in formula (I) represents a hydrogen atom, and Q represents a group represented by formula (II), is preferable. That is, an aryloxyacetamide compound represented by formula (IV) is preferable.
• R 1a , R 2 -R 5 , X, n, and Z are as defined in formula (I) and formula (II).
• the salt of the compound of the present invention is an agriculturally and horticulturally allowable salt.
• the salt include salts of inorganic acids such as hydrochloric acid or sulfuric acid; salts of organic acids such as acetic acid or lactic acid; salts of alkaline metals such as lithium, sodium or potassium; salts of alkaline earth metals such as calcium or magnesium; salts of transition metals such as iron or copper; and, salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine or hydrazine.
• the salts of the aryloxyacetamide compound can be produced by generally-known methods.
• An aryloxyacetate compound represented by formula (3) (hereinafter, may be referred to as “compound (3)”) is obtained by reacting a haloaryl compound represented by formula (1-1) (hereinafter, may be referred to as “compound (1-1)”) with an ester compound represented by formula (2-1) (hereinafter, may be referred to as “compound (2-1)”) in the presence of a base.
• a haloaryl compound represented by formula (1-1) hereinafter, may be referred to as “compound (1-1)”
• an ester compound represented by formula (2-1) hereinafter, may be referred to as “compound (2-1)”
• an aryloxyacetic acid compound represented by formula (4) (hereinafter, may be referred to as “compound (4)”) is produced by hydrolyzing the resulting compound (3).
• the amount of compound (2-1) is generally 1 to 2 mol, and preferably 1.0 to 1.2 mol with respect to 1 mol of compound (1-1).
• reaction may be performed in the absence of a base, it is preferable to perform the reaction in the presence of a base.
• a base examples include pyridine, triethylamine, potassium hydroxide and the like.
• the amount of the base is generally 1 to 2 mol with respect to 1 mol of compound (1-1).
• the reaction may be performed in a solvent.
• the solvent include ether type solvents such as dioxane, 1,2-dimethoxyethane, tetrahydrofuran; aromatic hydrocarbon type solvents such as toluene, benzene, xylene; aliphatic hydrocarbon type solvents such as n-pentane, n-hexane, n-heptane; halogenated hydrocarbon type solvents such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane; amide type solvents such as N,N-dimethyl formamide, N,N-dimethyl acetamide, N-methyl pyrrolidone; nitrile type solvents such as acetonitrile, benzonitrile; and mixed solvents including two or more of these solvents; and the like.
• the amount of the solvent it is inactive against the reaction.
• the solvent include ether type solvents such as diox
• the reaction temperature ranges from ⁇ 20° C. to the boiling point of the solvent. Although the reaction time varies according to the reaction scale, it is generally from minutes to hours.
• the hydrolysis can be performed by ordinary methods, it is preferable to perform in the presence of a base.
• the base include a metal hydroxide and the like, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or the like.
• the amount of the base is generally 1 to 20 mol with respect to 1 mol of compound (3).
• the reaction may be performed in a solvent.
• the solvent there are no particular limitations on the solvent provided it is miscible with water and inactive against the reaction.
• examples of the solvent are the same as the examples of the solvent used for producing compound (2).
• the amount of the solvent it is generally 1 to 100 ml with respect to 1 g of compound (3).
• the reaction temperature ranges from room temperature to the boiling point of the solvent. Although the reaction time varies according to the reaction scale, it is generally from minutes to hours.
• compound (6) An aryloxyacetamide compound represented by formula (6) (hereinafter, may be referred to as “compound (6)”) is produced by reacting compound (4) with a compound represented by formula (5) (hereinafter, may be referred to as “compound (5)”).
• compound (5) is an amine compound represented by formula (5-1) (hereinafter, may be referred to as “compound (5-1)”) or a sulfoximine compound represented by formula (5-2) (hereinafter, may be referred to as “compound (5-2)”).
• the amount of compound (5) is generally 1 to 2 mol, and preferably 1.0 to 1.2 mol with respect to 1 mol of compound (4).
• the reaction may be performed in a solvent.
• the solvent there are no particular limitations on the solvent provided it is inactive against the reaction.
• examples of the solvent are the same as the examples of the solvent used for producing compound (2).
• the amount of the solvent it is generally 1 to 100 ml with respect to 1 g of compound (4).
• a base when performing a reaction with compound (5-2), it is preferable to perform in the presence of a base.
• the base include pyridine, triethylamine, potassium hydroxide and the like.
• the amount of the base is generally 1 to 2 mol with respect to 1 mol of compound (4).
• the reaction temperature ranges from room temperature to the boiling point of the solvent. Although the reaction time varies according to the reaction scale, it is generally from minutes to hours.
• Compound (3) is obtained by reacting a hydroxyaryl compound represented by formula (1-2) (hereinafter, may be referred to as “compound (1-2)”) with an ester compound represented by formula (2-2) (hereinafter, may be referred to as “compound (2-2)”) in the presence of a base.
• the amount of compound (2-2) is generally 1 to 2 mol, and preferably 1.0 to 1.2 mol with respect to 1 mol of compound (1-2).
• reaction may be performed in the absence of a base, it is preferable to perform the reaction in the presence of a base.
• a base examples include pyridine, triethylamine, potassium hydroxide and the like.
• the amount of the base is generally 1 to 2 mol with respect to 1 mol of compound (1-2).
• the reaction may be performed in a solvent.
• the solvent include ether type solvents such as dioxane, 1,2-dimethoxyethane, tetrahydrofuran; aromatic hydrocarbon type solvents such as toluene, benzene, xylene; aliphatic hydrocarbon type solvents such as n-pentane, n-hexane, n-heptane; halogenated hydrocarbon type solvents such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane; amide type solvents such as N,N-dimethyl formamide, N,N-dimethyl acetamide, N-methyl pyrrolidone; nitrile type solvents such as acetonitrile, benzonitrile; and mixed solvents including two or more of these solvents; and the like.
• the amount of the solvent it is inactive against the reaction.
• the solvent include ether type solvents such as diox
• the reaction temperature ranges from ⁇ 20° C. to the boiling point of the solvent. Although the reaction time varies according to the reaction scale, it is generally from minutes to hours.
• the structure of the target compound can be identified and confirmed by a known analysis such as IR spectroscopy, NMR spectroscopy, mass spectroscopy or elementary analysis.
• the aryloxyacetamide compound or salt thereof according to the present invention is effective to prevent various pests (including acarus). In particular, it is effective as an acaricide.
• an acaricide including the compound of the present invention as an active ingredient. Since the compound of the present invention has insecticidal action on adult insects, immature insects, larvae, insect eggs and the like, it can be used to prevent harmful organisms such as acari present on agricultural crops. In particular, the acaricide has a superior prevention effect against acari present on agricultural crops, fruit trees, flowers and ornamental plants, and trees.
• (b) Acari belonging to the Tenuipalpidae family, for example, Brevipalpus lewisi, Brevipalpus russulus, Brevipalpus obovatus and Brevipalpus phoenicis of Brevipalpus spp.; for example, Tenuipalpus pacificus and Tenuipalpus zhizhilashviliae of Tenuipalpus spp.; and others such as Dolichotetranychus floridanus;
• (c) Acari belonging to the Eriophyidae family, for example, Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae and Aceria zoysiea of Aceria spp.; for example, Eriophyes chibaensis and Eriophyes emarginatae of Eriophyes spp.; for example, Aculops lycopersici and Aculops pelekassi of Aculops spp.; for example, Aculus fockeui, Aculus Mattendali , which belong Aculus spp.; and others such as Colomerus vitis, Calepitrimerus vitis, Phyllocotruta citri, Paracalacarus podocarpi, Calacarus carinatus, Acaphylla theavagrans, Paraphytoptus kikus, Epitri
• the acaricide including the compound of the present invention has a superior prevention effect against acarus parasitic on animals (prevention of ectoparasite).
• acarus parasitic in animals include those acarus which are parasitic in the back, armpit, underbelly, and inner thigh of host animals to obtain nutritional sources such as blood, dandruff from the animals to live.
• Examples of the host animals include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; pet birds (for example, pigeon, parrot, magpie, java sparrow, parakeet, bengalee, canary); cows, horses, pigs, sheep, goats; poultry (for example, ducks, chickens, quails, geese); bees (for example, apis mellifera , Japanese honey bee); and the like.
• pet birds for example, pigeon, parrot, magpie, java sparrow, parakeet, bengalee, canary
• poultry for example, ducks, chickens, quails, geese
• bees for example, apis mellifera , Japanese honey bee
• (b) Acari belonging to the Ixodidae family, for example, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicornis, Haemaphysalis mageshimaensis, Haemaphysalis yeni, Haemaphysalis campanulata, Haemaphysalis pentalagi, Haemaphysalis flava, Haemaphysalis megaspinosa, Haemaphysalis japonica and Haemaphysalis douglasi of Haemaphysalis spp.; for example, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amb
• (b) Acari belonging to the Sarcoptidae family, for example, Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes equi and Sarcoptes suis of Sarcoptes spp.; for example, Notoedres cati , which belongs to Notoedres spp.;
• the compound of the present invention may be used to prevent harmful organisms such as pests other than acari present on agricultural crops, sanitary pests, stored grain pests, clothes pests and household pests.
• Lepidopteran pests for example, Spodoptera litura, Mamestra brassicae, Agrotis ipsilon, Autographa nigrisigna, Plutella xylostella, Adoxophyes honmai, Homona magnanima, Carposina sasakii, Grapholitha molesta, Phyllocnistis citrella, Caloptilia theivora, Phyllonorycter ringoniella, Lymantria dispar, Euproctis pseudoconspersa, Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilalis, Hyphantria cunea, Cadra cautella, Heliothis spp., Helioverpa, Agrotis spp., Tinea translucens, Cydia pomonella, Pectinophora gossypiella , or the like;
• Hemipteran pests for example, Myzus persicae, Aphis gossypii, Lipaphis erysimi, Rhopalosiphum padi, Riptortus clavatus, Acrosternum hilare, Unaspis yanonensis, Pseudococcus comstocki, Trialeurodes vaporariorum, Bemisia tabaci, Bemisia argentifolii, Psylla pyricola, Stephanitis nashi, Nilaparvata lugens, Laodelphax stratella, Sogatella furcifera, Nephotettix cincticeps , or the like;
• Coleopteran pests for example, Phyllotreta striolata, Aulacophora indica, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Sitophilus oryzae, Callosobruchus chinensis, Popillia japonica, Anomala rufocuprea, Diabrotica spp., Lasioderma serricorne, Lyctus brunneus, Monochamus alternatus, Anoplophora malasiaca, Agriotes spp., Epilachna vigintioctomaculata, Tenebroides mauritanicus, Anthonomus grandis , or the like;
• Dipteran pests for example, Bactrocera cucurbitae, Bactrocera dorsalis, Delia platura, Hydrellia griseola, Drosophila melanogaster , or the like;
• Blattodea pests for example, Blattella germanica, Periplaneta fuligginosa, Periplaneta japonica, Periplaneta americana, Periplaneta australasiae , or the like;
• Plant parasitic nematodes for example, Meloidogyne incognita, Pratylenchus spp., Heterodera glycines, Aphelenchoides besseyi, Bursaphelenchus xylophilus , or the like.
• the pesticide including the compound of the present invention has a superior prevention effect against pests parasitic on animals (prevention of ectoparasite).
• Louse belonging to Haematopinidae family Louse belonging to Linognathidae family, Biting louse belonging to Menoponidae family, Biting louse belonging to Philopteridae family, Biting louse of Trichodectidae family;
• Flea belonging to Pulicidae family for example, Ctenocephalides canis and Ctenocephalides felis of Ctenocephalides spp.; Flea belonging to Tungidae family, Flea belonging to Ceratophyllidae family, Flea of Leptopsyllidae family;
• Mosquito belonging to Culicidae family Black fly belonging to Simuliidae family, Punkie belonging to Ceratopogonidae family, Fly belonging to Tabanidae family, Fly belonging to Muscidae family, Glossina belonging to Glossinidae family; Fly belonging to Hippoboscidae family, Fly belonging to Calliphoridae family, Fly belonging to Oestridae family;
• the compound of the present invention causes little chemical damage, demonstrates low levels of toxicity in fish and warm-blooded animals, and has a particularly high degree of safety.
• the pest control agent of the present invention contains as an active ingredient at least one type of compound selected from the compounds of the present invention.
• the pest control agent of the present invention may only contain the compound of the present invention, it may also contain carriers such as a solid carrier, liquid carrier or gaseous carrier.
• the pest control agent of the present invention may have the compound of the present invention impregnated in a base material such as a porous ceramic plate or non-woven fabric.
• a surfactant or other adjunct may be added as necessary.
• the pest control agent according to the present invention can be formulated into a form able to be typically adopted in agricultural chemicals, namely in the form of a water-dispersible powder, granules, powder, emulsion, water-soluble powder, suspension, granular water-dispersible powder, flowable preparation, microcapsules, aerosol, fog, heat transpiration agent, fumigant or poison bait.
• additives and carriers used when formulating a solid preparation include vegetable powders such as soybean powder or flour, mineral fine powders such as diatomaceous earth, apatite, plaster, talc, bentonite, pyrophillite or clay; and organic and inorganic compounds such as sodium benzoate, urea or sodium sulfate.
• solvents used when formulating liquid preparations include kerosene, xylene, and petroleum-based aromatic hydrocarbon, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohols, acetone, trichloroethylene, methyl isobutyl ketone, mineral oils, vegetable oils and water.
• Examples of the base materials of poison bait include bait components such as grain powder, vegetable oil, sugar or crystalline cellulose, antioxidants such as dimethylhydroxytoluene or nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, accidental swallowing preventives for small children and pets such as cayenne pepper powder, insect-attracting fragrances such as cheese fragrance or onion fragrance.
• bait components such as grain powder, vegetable oil, sugar or crystalline cellulose
• antioxidants such as dimethylhydroxytoluene or nordihydroguaiaretic acid
• preservatives such as dehydroacetic acid
• accidental swallowing preventives for small children and pets such as cayenne pepper powder
• insect-attracting fragrances such as cheese fragrance or onion fragrance.
• a surfactant can be added according to need in order to obtain a uniform and stable form during formulation.
• surfactants include nonionic surfactants such as polyoxyethylene alkyl phenyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene sorbitan higher fatty acid esters or polyoxyethylene tristyryl phenyl ethers; sulfate esters of polyoxyethylene alkyl phenyl ethers, alkyl benzene sulfonate, higher fatty alcohol sulfate, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkylnaphthalene sulfonates and isobutylene-maleic anhydride copolymers.
• the amount of the compound of the present invention contained in the preparation is preferably 0.01 to 90% by weight, and more preferably 0.05 to 85% by weight.
• the water-dispersible powder, emulsion, flowable preparation, water-soluble powder, granular water-dispersible powder which are obtained in this manner can be prepared in the form of a solution, suspension or emulsion and diluted with water to a prescribed concentration to spray onto plants or soil, or in the case of using them in the form of powder or granules, they can be sprayed directly onto plants or soil.
• a preparation that is supplied in the form of oil solution, aerosol, fog, poison bait or miticidal sheet can be directly used.
• the compound of the present invention can be used at a ratio of 0.01 mg to 1000 mg per 1 kg of host animal.
• An acaricide for preventing acari can be applied using a known veterinary method.
• Such methods include methods in which the acaricide is administered to an animal by a tablet, capsule, immersion liquid, food additive, suppository or injection (intramuscular, subcutaneous, intravenous or intraabdominal injection) when administered for the purpose of systemic control, methods in which an oily or aqueous liquid preparation is administered by spraying, pouring on or spotting on when administered for the purpose of non-systemic control, and methods in which the acaricide is mixed with a resin and the kneaded product is molded into a suitable shape such as that of a collar or ear tag which is then attached to the animal.
• the pest control agent of the present invention can be mixed or combined with fungicides, other insecticides or acaricides, nematocides, soil pesticides, plant regulators, synergists, fertilizers, soil improvers or animal feeds and the like.
• Insecticides Insecticides, acaricides, nematocides, soil pesticides and antiparasitic agent:
• organic (thio)phosphate-based such as acephate, azamethiphos, azinphos-methyl, azinphos-ethyl, bromophos-ethyl, bromfenvinphos, BRP, chlorpyriphos, chlorpyriphos-methyl, chlorpyrifos-ethyl, chlorfenvinphos, cadusafos, carbophenothion, chlorethoxyfos, chlormephos, coumaphos, cyanofenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, demeton-S-methyl, dimethylvinfos, demeton-S-methyl sulphone, dialifos, diazinon, dichlofenthion, dioxabenzofos, disulfoton, ethion, ethoprophos, etrimfos, EPN, f
• chitin synthesis inhibitors chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, bistrifluron, nobifumuron, buprofezin, hexythiazox, etoxazole, clofentezine, fluazuron, penfluron;
• ecdysone antagonists halofenozide, methoxyfenozide, tebufenozide, chromafenozide, azadirachtin;
• juvenile hormone-like substances pyriproxyfen, methoprene, diofenolan, epofeneonane, hydroprene, kinoprene, triprene;
• lipid biosynthesis inhibitors spirodiclofen, spiromesifen, spirotetramat, flonicamid;
• nicotine receptor agonist/antagonist compounds acetamiprid, clothianidine, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap; flupyradifurone;
• organochlorine compound camphechlore, chlordane, endosulfan, HCH, ⁇ -HCH, heptachlor, methoxychlor;
• macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, ivermectin, seramectin, doramectin, epinomectin, moxidectin; milbemycin; milbemycin oxime;
• METI I compounds fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenirim, hydramethylnon, fenpyroxymate, pyrimidifen, dicofol;
• METI II and III compounds acequinocyl, fluacrypyrim, rotenone;
• oxidative phosphorylation inhibitor compounds cyhexitin, diafenthiuron, fenbutatin oxide, propargite, azocyclotin;
• sodium channel blocker compounds indoxacarb, metaflumizone;
• microbial pesticides BT agents, insect pathogen viral agents, insect pathogen fungal agents, nematode pathogen fungal agents, bacillus, beauveria bassiana, metarhizium anisopliae, paecilomyces, thuringiensin, verticillium;
• latrophilin receptor agonist depsipeptide, cyclodepsipeptide, 24-membered cyclodepsipeptide, emodepside;
• ryanodine derivative agonist flubendiamide, chlorantraniliprole, cyantraniliprole;
• magnesium-stimulated ATPase inhibitor thiocyclarm, thiosultap, nereistoxin
• antifeedant pymetrozine
• acari growth inhibitor clofentezine, etoxazole
• benzimidazoles fenbendazole, albendazole, triclabendazole, oxibendazole;
• benzimidazole-based benomyl, carbendazim, fuberidazole, thiabendazole, methyl thiophanate; chlorfenazole;
• dicarboxyimide-based fungicides chlozolinate, iprodione, procymidone, vinclozolin;
• DMI fungicides imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, triforine, pyrifenox, fenarimol, nuarimol, azaconazole, bitertanol, bromconazole, cyproconazole, difenoconazole, diniconazole, epoxyconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipuconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, etaconazole, furconazole-cis; diclobutrazol, diniconazole-
• phenylamide-based benalaxyl, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, ofurace; benalaxyl-M, clozylacon;
• amine-based aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidine, piperalin, spiroxamine;
• carboxamide-based benodanil, boscalid, carboxin, fenfuran, flutolanil, furametpyr, mepronil, oxycarboxin, penthiopyrad, thifluzamide; bixafen, isopyrazam, penflufen, fluxapyroxad, Sedaxan;
• AP fungicides anilinopyrimidines-based: cyprodinil, mepanipyrim, pyrimethanil or the like; andoprim;
• QoI fungicides QoI fungicides (Qo inhibitor-based): azoxystrobin, picoxystrobin, pyraclostrobin, kresoxim-methyl, trifloxystrobin, dimoxystrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, metominofen; ametoctradin, pyrametostrobin, pyraoxystrobin, pyribencarb; coumethoxystrobin, coumoxystrobin, enestroburin, fenoxystrobin, triclopyricarb;
• PP fungicides phenylpyrrole-based: fenpiconil, fludioxonil;
• AH fungicides aromatic hydrocarbon-based: biphenyl, chloroneb, dichloran, quintozene, tecnazene;
• MBI-R-based fthalide, pyroquilon, tricyclazole
• MBI-D-based carpropamid, diclocymet, fenoxanil
• SBI agents fenhexamid, pyributicarb, terbinafine
• Qil fungicides Qi inhibitors: cyazofamid; amisulbrom, furmecyclox;
• organic tin compounds triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide;
• phosphate esters phosphonic acid, tolclofos-methyl, fosetyl; tolctophos-methyl;
• CAA fungicide (carboxylic amide)-based: dimethomorph, flumorph, benthiavalicarb-isopropyl, iprovalicarb, mandipropamide; valifenalate;
• plant growth regulators examples include:
• abscisic acid indole butyric acid, uniconazole, ethychlozate, ethephon, cloxyfonac, chlormequat, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac-ethyl, mepiquat-chloride, paclobutrazol, paraffin wax, piperonyl butoxide, pyraflufen ethyl, flurprimidol, prohydrojasmon, prohexadione-calcium, benzylaminopurine, pendimethalin, forchlorfenuron, potassium hydrazide maleate, 1-naphthylacetoamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethychlozate, butralin, 1-methylcyclopropene, aviglycine hydrochloride.
• 0.18 g of compound 5 was dissolved in 15 ml of acetonitrile. 0.11 g of 2-(pyridine-2-yl)propane-2-amine, 0.15 g of 1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride, 0.08 g of 1-hydroxybenzotriazole, and 0.11 g of triethylamine were added to the resulting solution, followed by stirring overnight at room temperature. Water was then added to the resulting solution, followed by extracting with ethyl acetate. The resulting organic layer was dried by adding magnesium sulfate and filtered, followed by distilling the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 0.16 g of compound 6 (yield: 67%) having a melting point of 123 to 125° C.
• TABLES 1 to 3 show only a part of aryloxyacetamide compounds of the present invention.
• composition examples of the pest control agent according to the present invention are shown below. However, additives and addition ratios are not limited to the preparation examples, and can be modified over a wide range. Moreover, the term “parts” used in the preparation examples indicates “weight parts.” The following are the preparation examples for agricultural and horticultural use.
• Compound of the present invention 40 parts Diatom earth 53 parts Fatty alcohol sulfate 4 parts Alkylnaphthalene sulfonate 3 parts
• the compound of the present invention was dissolved in an organic solvent, and sprayed on a carrier, followed by evaporating the solvent under reduced pressure.
• This kind of granulated powder may be mixed with animal food.
• the impregnating agent was filter-sterilized by a sterilizing filter after adjustment.
• test examples demonstrate that the compound of the present invention is useful as an active ingredient of acaricide.
• the aforementioned test was carried out on the emulsions containing the Compound Nos. 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-11, 1-13, 1-14, 1-16, 1-17, 1-18, 1-25, 1-28, 1-29, 1-30, 1-31, 1-34, 1-39, 1-40, 1-41, 1-42, 1-43, 2-1, 2-2, 2-3, 2-6, 2-7, 2-11, 2-16, 2-24, 2-25, and 2-28.
• the insect mortality rates after 3 days and 10 days for all of the compounds were 90% or higher.
• the aryloxyacetamide compound or salt thereof according to the present invention can protect agricultural crops against infection by harmful organisms. In addition, it also has hygiene applications. Particularly, the compound of the present invention is able to effectively reduce acarus.

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